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Dihydroactinidiolide

Dihydroactinidiolide

IUPAC name	(7aR)-5,6,7,7a-Tetrahydro-4,4,7a- trimethyl-2(4H)-benzofuranone
Other names	Dihydroactinidiolide
Identifiers
CAS number	17092-92-1
SMILES	O=C2O[C@]1(C)CCCC(C)(C)C1=C2
Properties
Molecular formula	C₁₁H₁₆O₂
Molar mass	180.24 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Dihydroactinidiolide is a volatile terpene. It has a sweet, tea-like odor and is used as a fragrance. Dihydroactinidiolide occurs naturally in black tea, fenugreek, fire ants, mangos, silver vine, and tobacco. It has also been prepared synthetically.^[1]

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Dihydroactinidiolide is a pheromone for a variety of insects;^[2] for example, it is one of the three components of the pheromone for queen recognition of the workers of the red fire ant.^[3]

As with nepetalactone, found in catnip, dihydroactinidiolide is a cat attractant. Cultivators of silver vine (which contains another such chemical, actinidine, which is also a cat attractant) sometimes find their plants destroyed by enthusiastic cats.

References

^ S. Yao, M. Johannsen, R.G. Hazell, K.A. Jorgensen, J. Org. Chem., 63, 118-121.
^ Pherobase listing for dihydroactinidiolide
^ Rocca, J.R. Tumlinson, J.H., Glancey, B.M., Lofgren, C.S., Tetrahedron Lett., 1983, 24, 1889.

Categories: Terpenes and terpenoids | Oxygen heterocycles | Pheromones